


When in Doubt, Wear Red

by mercurialMalcontent



Category: Homestuck
Genre: Crossdressing, Gen, Genderbending
Language: English
Status: Completed
Published: 2011-06-09
Updated: 2011-06-25
Packaged: 2017-10-20 07:03:03
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 3,195
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/210035
Author URL: https://archiveofourown.org/users/mercurialMalcontent/pseuds/mercurialMalcontent
Summary: <blockquote class="userstuff">
              <p>'There was only one thing worse than Dave Strider's smug motherfucker act, and it was his smug motherfucker act after he'd won a bet.'</p><p>In which Karkat has lost a bet to Dave and turns paying up into payback.</p>
            </blockquote>





	1. The Gambit

There was only one thing worse than Dave Strider's smug motherfucker act, and it was his smug motherfucker act after he'd won a bet.

It was worse than Sollux's smug, worse than even Vriska's smug -- at least spiderbitch had the fucking grace to have visible emotions. But no, even the hint of a smirk or a glance over his glasses was too good for Dave Fucking Strider, asshole at large. He just stood there, hands in pockets, those big dark glasses boring into Karkat's soul as he waited for the troll to crack.

As he always did. " _What_ ," Karkat snapped, his fingers reflexively curling into fists. "What do you want. Get it over with. Tell me what disgusting human thing you want me to do so we can get our obligatory Laugh at Karkat time over with and I can go die in peace."

"You can't die anymore," Dave said coolly, his posture not shifting even the most infinitesimal portion of a measuring unit.

"We're going to test that theory if you continue to tug on the thin fucking shreds that are left of whatever patience I still have, nookstain," Karkat snarled. "Spit it out! WHAT. DO. YOU. WANT."

Was that a snort he heard? Did the way Dave push his glasses up on his nose denote amusement? Was he going to fucking respond before Karkat spontaneously exploded and blew a hole into this pathetic excuse for an afterlife they were all suffering through?

From a far corner, Rose sighed and looked up from her omnipresent knitting. "Dave, please tell him before the heat death of this universe."

"Nah."

Rose's icy lavender eyes slid to Karkat, who gave the mouthy broad the full force of his infuriated glare. She sighed again. "Then tell him before he causes the heat death of this universe."

Dave gave her a coolkid shrug that Karkat wanted to punch him in the face for. "Alright. Wouldn't want Karkitty's head to explode all over our nice shiny new universe."

"THE ONLY THING THAT IS GOING TO EXPLODE--"

"Whoa, whoa, whoa, hold up there," Dave said, one hand shooting up to stop Karkat's forward progress. Karkat stopped, not willing to give the insufferable prick the satisfaction of actually touching Karkat's garments with his pasty white flesh. "You get up in my grill, you owe me extra."

Karkat ground his teeth. "I'm not interested in your fucking retarded meat-burning apparatus. Why did you even have those things? Didn't your species ever invent temperature regulated cooking boxes, or were you too busy licking each other's seed flaps to raise to that basic level of technology?"

An honest-to-gog snort from the corner. "Maybe you shouldn't stop. He's on a roll."

Karkat shot Little Miss Meddlesome a _look_ as Dave did that little tilt of his head that suggested he was giving his paradox sister one hell of a side-eye.

"Alright, so," the coolkid said, pointing his stone face back at Karkat, "tomorrow, from the time you come out of your room until _I_ feel like saying goodnight, you pretend you're a girl."

Karkat had braced himself for some sort of searing stupidity, but this left him in baffled incomprehension. The poisonous look he caught Rose leveling on her brother only confused him more. "Which one?"

Dave's little smirk vanished. "What?"

"Which one, fuckass? I'd like to know who I'm supposed to grovel to the day after tomorrow once I've cosplayed as them for your twisted human amusement." A thought flitted through Karkat's head that instantly made him bare his teeth. "And if you expect us to make out, fuck you, pervert."

If Karkat wasn't mistaken (and it'd be hard to be given the maggoty translucence of the human's skin), a blush was creeping across Dave's cheeks. "You're missing the point, dunkass. I don't want you to be a particular girl, I want you to be _a_ girl. Skirts. Ruffles. Lipstick. Be the pretty little lolita we all know you've got deep inside, Karkitty."

"What the fuck is a lolita?" Karkat snarled, his mouth running off before his mind parsed the far more disturbing implication in Dave's words. However. he didn't have a chance to shout about it before Rose spoke up again.

"What my dear brother is referring to is the backward and dated human concept that certain articles of clothing belong only to certain genders--"

"You're fucking kidding me, that's a _thing_?"

"--and that it is inherently humiliating for a man to dress in clothing that has been assigned for women."

Karkat looked from Rose, who still glared at her brother, to Dave, who looked, insofar as it was possible for the coolkid to have expressions, like he desperately wanted to abscond. "Why the fuck is that a thing? Oh my god." Karkat threw up his hands. "I can't believe we made your universe. It was the stupidest of all possible universes. It had all of the stupid! But it couldn't have had all of it or I wouldn't be standing here after having been asked to participate in something stupid from it. I am going to explode from stupidity _right on this very spot_."

"Says the man from a planet where pictures of horse dick are fine art."

"Strider, don't even start with me, I've seen your Internet."

"Touché," said Rose, her voice razor-edged. "Which means that you can also look up the intricacies of human female fashion. I'd let Dave explain it to you, but," she said as she stood, her knitting vanishing into her sylladex with an audible snap, "he and I need to have a what I believe your species calls a 'feelings jam'."

"Fuck," Dave muttered. He flashstepped from the room, Rose lunging after him.

carcinoGeneticist [CG] began trolling grimAuxiliatrix [GA]

CG: KANAYA. I NEED A FAVOR.   
GA: Do You Need To Hide A Body   
CG: NOT THAT KIND OF A FAVOR.   
GA: Then Do You Need Me To Help You Make One   
CG: THAT ISN'T FUNNY.   
GA: Heh  
GA: Sorry  
GA: If Its Auspisticing Im Sorry But I Dont Do That Anymore   
CG: NO, NO, NONE OF THAT.  
CG: I NEED A DRESS.  
CG: ... KANAYA?


	2. The Plan

**Summary for the Chapter:**

> In which Karkat tells Kanaya his plight, and comes up with a plan.

"I'm curious as to why you need a dress, but I'm a little afraid to ask," Kanaya said as she let Karkat into her workroom.

"That's pretty funny coming from the person who asked me if I needed help murdering someone," Karkat grumbled as he picked his way through the strewn bolts of bright fabrics and scattered sewing supplies. "I lost a bet."

"... Why would Vriska want you to wear a dress?"

"Give me a little credit, Kanaya, I didn't bet against her. I'm not fucking stupid." Karkat looked around and scowled at the complete lack of places to sit. Well, there was a pile of pillows, but piles of things made him think of feelings jams and that was a big bowl of no fucking thank you right there. "I lost to Strider."

"That wasn't very smart either," Kanaya said primly as she picked her way over to her sewing desk.

"Thanks a _lot_."

Kanaya gave him a mild little smile that he would have found infuriating from anyone else. "I confess I'm at a loss as to why Dave would want you to wear a dress." She tilted her head. "Unless he wants to embarrass you by making you imitate Eridan?"

Karkat shuddered. "No, thank fucking god." Eridan had, in 'penance' for his actions in their former life, taken to moping around in some ridiculous confection of white drapery that involved a lot of lace, crying endlessly, and swooning in corners like a particularly stupid ghost. "I don't know why you helped that wet bulgemunch alchemize that getup."

"It was worth it to watch him tremble and stammer every time I looked at him," Kanaya said with another one of those smiles.

"Every day I find something new to admire you for."

"I will take that as genuine since you didn't say fuck even once." She smiled more widely at Karkat's attempts not to smile, himself. "Now, sit down," she said, gesturing at the pillow pile, "and tell me why Dave has required you to wear a dress."

The almost-smile fell right off of Karkat's face. "Oh god, not the fucking pillow pile."

"Yes, the pillow pile," Kanaya said grandly. She rose and took his arm. "We need to have--"

"Please don't say a feelings jam--"

"A tactical strategy meeting."

Piles of things weren't so bad when they were used for tactical strategy meetings, especially when the pile was this cozy. Karkat nestled in with a grumpy sigh as Kanaya curled up nearby. "It's not just the dress," he said, picking at a tassel. "He wants me to, quote, be a girl, unquote."

Kanaya stilled beside him. "Be a girl?"

"Not literally!" Karkat bit his tongue on the 'I think' that wanted to follow and gave Kanaya a sidelong look. "Strider wants me to participate in the pathetically backwards and apparently humiliating human tradition of making a man wear a woman's clothes."

"How is that a thing?"

Karkat related what Lalonde had told him, making sure to emphasize the stupidity with plenty of exasperated gestures. Kanaya didn't look nearly as horrified or angry as he thought she should have; by the time he finished, her frown was more thoughtful than anything. "I wonder if it has anything to do with their particular sexual dimorphism." She tapped her lip with a neatly manicured finger. "However, females aren't pregnant all of the time so it seems pretty arbitrary."

"Pretty fucking _stupid_ , you mean."

Kanaya quirked. "That too. Did Dave specify to you the exact nature of the stupidity he requires you to indulge him in?"

"He said something about 'being the pretty little lolita I am deep inside'." Karkat made a face and slouched further down into the pillows. "Whatever the fuck a lolita is."

"Hm... I believe Jade mentioned it once." Kanaya materialized her lunchtop from her sylladex and balanced it on one of the pillows in front of her. A few moments later she had brought up a collection of images on the projected screen. "I am under the impression that the style means to convey a sense of innocence and purity..."

But Karkat wasn't listening. He was staring in fascinated horror at the layers of frills and lace and pink. "There is NO FUCKING WAY I'm going to wear something that makes me look like a mound of human baked confectionery!"

"I thought you liked human baked confectionery."

"STOP CHANGING THE SUBJECT." Oh god, if it was any other troll sitting there smirking at him like that Karkat would flip his shit so hard they wouldn't even know what hit them, but since it was his good friend and only hope he scowled and shifted his way deeper into the pillows. "I'm just going to pretend Strider never brought up that lolita shit and wear something that isn't a monumental fucking embarrassment."

"W-well," Kanaya said, failing to entirely choke back a giggle at his expense, "that may be difficult. Female human fashion that isn't childish frippery seems centered around enhancing female secondary sexual characteristics." She eyed Karkat's chest. "Which you have a complete lack of."

"Oh my god. Look. Look at me and how much I don't care. See me rolling my eyes?" He jabbed a finger at his face. "See how hard I'm rolling them? How hard I roll them would be directly proportional to how much I don't care except that if I roll them any harder they're going to fucking fall out and then we'll have three blind psychos running around this sorry excuse for an afterlife. So spare me."

"I'll try my best," Kanaya said, sounding like she wasn't going to try very hard at all.

"You'd better," Karkat grumbled without any force whatsoever. "Besides, you're wrong."

"How would you know if I'm wrong on something to do with fashion?"

"Because I'm the one who's been forced to sit through John's shitty human movies. Give me the lunchtop."

'Forced' was an exaggeration, really. Coaxed, perhaps. Urged, maybe. Or possibly Karkat had stomped up to John one day and told him, "Let's get this over with -- show me your stupid human movies before you spring them on me like a trap and give me an aneurysm because I was caught totally unprepared for the true depths of their shittiness." John had, predictably, been delighted.

But that was neither here nor there. What mattered was that viewing all of those shitty human movies (and he'd viewed an imperial fuckton of the things, only to discover the dismaying fact that human cinematographic history spanned so little time) had given Karkat some insight into human fashion aesthetics. Not much, but enough for Karkat to be certain that, in the spectrum of what humans considered a pleasing female form, there was a range that a big-eyed, wiry troll boy would have very little trouble emulating with some creative costuming.

And in that range, there was one particular actress Karkat had in mind.

Kanaya stared at the stills from _Breakfast at Tiffany's_ Karkat had brought up. She looked from the images to Karkat and back again. "Yes, I see how that could work."

**Notes for the Chapter:**

> Yes, Karkat as Troll Audrey Hepburn. He is going to be so classy, you don't even _know_.


	3. The Payoff

**Notes for the Chapter:**

> Now with [adorable](http://i71.photobucket.com/albums/i139/omgIamBored/IMG_4265.jpg) [fanart](http://i71.photobucket.com/albums/i139/omgIamBored/IMG_4266.jpg) of [Karkat Hepburn](http://i71.photobucket.com/albums/i139/omgIamBored/IMG_4269.jpg) by qwopisinthemailbox!

Kanaya slipped into Karkat's room early the next morning, her sylladex loaded with the pieces of the outfit they had alchemized the night before. To his embarrassment she had to help him change (the filmy pseudopants called hose were downright diabolical), and once that was done she sat him down to put on the 'finishing touches'.

The finishing touches were far more of a trial than putting on hose, however. Karkat was pretty sure that in Kanaya's attempts to tame his hair with combs and hair pins into something other than its usual crow's nest she'd pulled out half of it. Almost worse was stuff she spackled his face with (to keep him, in her words, from looking like a three-day-old corpse, which was rich coming from a rainbow drinker), which felt disgusting and gave him the continual urge to paw at his face.

But then it was done, and after Karkat got a good look at himself in the full-length mirror Kanaya pulled from her sylladex, he had to admit that the suffering was worth it. He looked pretty goddamned good in that slinky black sheath and long black gloves, even with the sparkly bullshit draped around his neck and perched on his head. "I am going blow that fucking coolkid's mind."

Kanaya's reflection _smirked_ , and Karkat only remembered at the last second not to facepalm. "Clear those obscene blackrom thoughts from your head, okay, because we aren't done here." Karkat scowled at his reflection. "There's something missing,"

Kanaya tapped between his shoulder blades. "Good posture and a pleasant expression."

"Besides that," Karkat grumbled as he squared his shoulders. "As much as I hate to have you slather more spackle onto my face--"

"It's makeup."

"Whatever. The point is, black lips aren't going to do it." Sure, the monochrome effect Karkat sported -- aside from his horns and eyes -- made him look as if he'd just stepped off of the screen itself, but it wasn't _enough_. He needed something that would grab Strider's attention and squeeze it so hard he'd barely be able to breathe.

"Mm. I have many colors-- blue, green, a stunning shade of violet..." Kanaya's reflection tilted its head and frowned. "Somehow none of those seem correct."

Karkat shook his head, even though he felt pretty sure he knew what he needed. The color was, as far as he could tell, what human women gravitated toward when they wanted to make an impact. On Karkat, it'd stun the fuck out of everybody. Too bad it was a color he found personally embarrassing, but sometimes one just didn't have a choice.

"Since I'm doing a human thing, I might as well do it all the way." He turned Kanaya with a shrug. "When in doubt, wear red."

Kanaya's eyebrows shot up. Without a word, she retrieved a tube from her makeup box and painted his lips. "Suitable?" she asked when she finished.

Karkat looked, in his not so humble opinion, fucking glamorous. "Very."

 

Minutes later, Karkat trailed behind Kanaya down the hall to the cafeteria, growing further behind with every step. Okay, he looked amazing, but that didn't mean he wasn't a little nervous. Wearing what was essentially a long shirt and no pants was more than a little disarming, as was how standing up straight while wearing heels made his ass jut out. Kanaya's reassurance that it was a shapely ass did not help.

He jumped as he heard Strider's drawl, presumably spurred by Kanaya's arrival. "Our guest of honor is still missing? Someone needs to get his ass out of bed before I get it out for him."

Kanaya made some reply Karkat couldn't catch and Strider laughed. Karkat gritted his teeth and redirected the energy he'd usually spend tensing up into walking faster. "Delicate fucking flower, huh, should've guessed. Can't wait to see what frilly shit--"

Silence didn't so much descend as it clanged down like an imperial fuckton of lead bricks when Karkat stepped into the room. The full force of the attention of fifteen adolescent minds hit him like a thousand pouncing Nepetas all at once, and for half a second time slowed like a thick sticky substance in freezing weather. Karkat considered the option of turning and running like hell.

The glass in Strider's suddenly slack hand crashed to the floor. The tinkle of breaking glass, sweet and loud as a victory bell, rang time back to its normal pace. Karkat found himself still moving, right towards the coolkid, who was so transfixed he hadn't realized that he no longer held a glass, much less that the contents had splashed all over his sneakers.

_Yes._ Karkat stepped close and pulled Strider's stupid ironic shades down the bridge of his nose far enough to reveal how wide his freakish red eyes had gone.

_Hell_ yes. Karkat leaned closer, just short of the other boy's face blurring. "Am I enough of a girl for you now, fuckass?" he growled in a way that was maybe a little more of a purr than he thought he intended, but nevermind, because Strider's pupils dilated and he made a thin, choked noise in the back of his throat.

Hell _fucking_ yes. Karkat smirked and shoved those glasses back up Strider's nose hard enough to make the coolkid stumble back. "I am dying for a fucking pastry, here," Karkat announced as he turned away.

 

caligulasAquarium [CA] started trolling carcinoGeneticist [CG]

CA: hey kar you were lookin pretty fuckin good today  
CG: WHY DO YOU STILL EXIST. GO AWAY.  
CA: cant a guy pay a compliment to someone finally displayin some fuckin class  
CA: and youre one classy bitch kar  
CG: WHAT THE ACTUAL FUCK, ARE YOU HITTING ON ME  
CG: AGAIN???  
CA: no i just wwanna ask you somethin  
CG: THE ANSWER IS NO. THE ANSWER IS ALWAYS NO.  
CA: no no i swwear its just somethin small  
CA: can i borroww your dress

carcinoGeneticist blocked caligulasAquarium

**Notes for the Chapter:**

> Chapter artwork commissioned from the ever-fabulous [roachpatrol](http://roachpatrol.tumblr.com/post/47507664287/karkat-getting-all-dolled-up-from)!

**Author's Note:**

> My headcanon says that with female trolls not being tied by biology to reproduction, and given how there is no discernable (to me!) social gender division in canon, they wouldn't care about gender-segregating types of clothes.

**Works inspired by this one:**

  * [Karkat Hepburn](https://archiveofourown.org/works/374073) by [Applefroggie](https://archiveofourown.org/users/Applefroggie/pseuds/Applefroggie)




End file.
